Tag: M.W:100-200

Synthetic Route of C10H8ClN. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about Nucleophilic heteroaromatic substitution. XXVII. Piperidino dechlorination and methoxy dechlorination of 6- and 8-alkyl-4-chloroquinolines. Steric hindrance to specific solvation.

Kinetic data for the reaction of 6- and 8-alkyl-substituted 4-chloroquinolines with piperidine in four different solvents and with NaOMe in MeOH were obtained and compared. The tert-butyl group located at the position peri to the aza group is found to cause rate-depressing effects and significant increases in the energy and entropy of activation when the solvent is hydroxylic (methanol) whereas only minor changes are observed in aprotic or poor proton-donor solvents (toluene, HCONMe2, and piperidine). The results are interpreted in terms of steric inhibition of specific solvation (H bonding). 15 references.

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Safety of 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride, is researched, Molecular C8H12ClNO2, CAS is 148-51-6, about Effects of deoxpyridoxine on the formation and development of some experimental neoplasias. I. Ascites tumor in mice. Author is Grimaldi, T.; La Pesa, M.; Curci, E.; Semeraro, N..

I.p. or i.m. injection of the antivitamin B6 compound 4-deoxypyridoxine-HCl (I) [148-51-6] (0.07 mg/day) did not alter either the percentage of tumor take or the survival time of mice inoculated previously or subsequently with Ehrlich ascites tumor. The mice were not kept on a vitamin B6-deficient diet.

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4-Chloro-8-methylquinoline. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about Tricyclic heteroaromatic ring systems. II. A convenient synthesis of 1H-pyrrolo[3,2-c]quinolines. Author is Khan, Misbahul Ain; Ferreira de Rocha, Joao.

Quinol-4-yl hydrazones I (R = H, Me, Et; R1 = Me, Ph, Et; RR1 = (CH2)n, n = 3, 4; R2 = H, Me; R3 = H, 6-, 7-, 8-Cl, 6-, 7-, 8-Me, 6-, 7-, 8-MeO) on heating in high boiling solvents undergo cyclizations to give 1H-pyrrolo[3,2-c]quinolines II in good yields. Some of these I were alkylated to provide their N-alkyl derivatives

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Pathologica called Influence of some vitamin B6 antimetabolites on the induction and development of solid IRE reticulosarcoma in rats. I. Deoxypyridoxine, Author is La Pesa, M.; Grimaldi, T.; Curci, E.; Semeraro, N., which mentions a compound: 148-51-6, SMILESS is OC1=C(C)C(CO)=CN=C1C.[H]Cl, Molecular C8H12ClNO2, Quality Control of 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride.

Control and exptl. rats were inoculated s.c. in the dorsal region with solid reticulosarcoma IRE. Starting on the 2nd day, each exptl. rat received i.m. 0.35 mg/day of 4-deoxypyridoxine-HCl until death (14-32 days later). The values for latent period, survival, and daily body weight were similar for both groups.

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Category: pyrimidines. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride, is researched, Molecular C8H12ClNO2, CAS is 148-51-6, about Inhibition of growth and increased mortality of Mexican bean beetle larvae fed with thiamine and pyridoxine antagonists and reversal of effect with vitamin supplementation. Author is Gothilf, Shmuel; Waites, Robert E..

Repressed growth and survival of Mexican bean beetle (Epilachna varivestis) larvae were observed when the larvae were fed leaves dipped in 1% solutions of the vitamin analogs oxythiamine, pyrithiamine, or deoxypyridoxine. When the corresponding vitamins, thiamine or pyridoxine, were added to the antivitamins in a 1:1 ratio, the adverse effects of the antivitamins were reversed. Sulfanilamide and pantoyltaurine also increased mortality when used as 1% solutions, but pantothenyl alc., 2-picolinic acid, and 3-acetylpyridine were ineffective.

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-Bromo-3-methoxypropanoic acid, is researched, Molecular C4H7BrO3, CAS is 65090-78-0, about New and alternate synthesis of lacosamide with chemoenzymatic method, the main research direction is enzymic resolution racemic lacosamide; lacosamide enantiopure preparation.Recommanded Product: 65090-78-0.

Lacosamide [(R)-2-acetamido-N-benzyl-3-methoxy propionamide] 5 is a novel antiepileptic drug. Lacosamide was prepared by a chem. method with enzymic resolution of racemic lacosamide. Herein is reported an expedient four-steps enantioselective synthesis of lacosamide 5 beginning with Me 2,3-dibromo propionate 1. A new resolution process catalyzed by Novozyme 435. The products were obtained in very good yields and in a state of high purity. All the newly synthesized compounds (2-5) were characterized by their spectral (IR, 1H NMR, C13 NMR and MS) data.

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of vitamin B6 derivatives. Catalytic reduction of hydroxymethyl group substituted in pyridine ring》. Authors are Naito, Takeo; Ueno, Katsujiro.The article about the compound:5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloridecas:148-51-6,SMILESS:OC1=C(C)C(CO)=CN=C1C.[H]Cl).Category: pyrimidines. Through the article, more information about this compound (cas:148-51-6) is conveyed.

Catalytic reduction of 1.64 g. pyridoxine triacetate-HCl in 32 mL. H2O with 1 g. 10% Pd-C 1.5 h. at normal pressure of H absorbed 240 mL. H and gave 0.7 g. 3,4,6,5-Me3(OH)C5HN.HCl (I), m. 209-12°. Similarly, pyridoxine 4-Et ether HCl salt yielded 52% I, m. 210-12°. The above reaction with 1 mol absorption of H yielded 18% 4,6,3,5-Me2(HOCH2)(HO)C5HN.HCl (II), m. 250° (decomposition), and the mother liquor yielded 31% 3,6,4,5-Me2(EtOCH2)(HO)C5HN.HCl; picrate m. 138°. Catalytic reduction of 0.56 g. 6,3,4,5-Me(AcOCH2)(EtOCH2)(HO)C5HN.HCl in 20 mL. MeOH with 0.8 g. 10% Pd-C showed no absorption of H, the reduction proceeded well by addition of 20 mL. H2O and absorbed 54 mL. H in 2 h., and the product in 10% HCl heated 30 min. at 100° yielded 48.8% 3,6,4,5-Me2(EtOCH2)(HO)C5HN; picrate, m. 138°. Catalytic reduction of 3.76 g. pyridoxal oxime-HCl in 170 mL. H2O and 88 mL. 10% HCl with 4.8 g. 10% Pd-C absorbed 3050 mL. H in 20 h. and yielded 62% 3,6,4,5-Me2(HCl.H2NCH2)(HO)C5HN.HCl (III), m. 262-3° (decomposition); diacetate, C12H16O3N2, m. 176-7°; ditosylate-HCl, m. 194-5°. Catalytic reduction of 0.29 g. 6,3,4,5-Me(AcOCH2)(AcNHCH2)(AcO)C5HN in 8 mL. MeOH and 2.2 mL. 10% HCl-MeOH showed no absorption H but an addition of 10 mL. H2O absorbed 28 mL. H in 2 h. and yielded 100% diacetate of III, m. 174°. Similarly, 0.51 g. pyridoxal-HCl in 20 mL. H2O and 0.5 g. 10% Pd-C yielded 30% II, m. 246-8°. Catalytic reduction of 0.58 g. pyridoxal Et hemiacetal-HCl (IV) in 20 mL. EtOH and 0.5 g. 10% Pd-C (1 mol H absorbed) yielded 79% 6,5,3,4-Me(HO)(CH2OCH2)C5HN.HCl (V), m. 233-4°; picrate m. 186-7°. Similarly, 0.58 g. IV, 20 mL. H2O and 0.5 g. Pd-C yielded 40% II, m. 248-50°; 0.58 g. IV, 20 mL. HCl, 2.7 mL. 10% HCl and 0.5 g. Pd-C yielded 68% V, m. 225-30°. Catalytic reduction of 1.09 g. 2-HOCH2C5H4 N in 15 mL. MeOH and 51 mL. 5% HCl-MeOH with 1 g. Pd-C (260 mL. H absorbed in 2 h.) yielded 90% 2-MeC5H4N (VI); picrate m. 164-5°. Similarly, 1.23 g. 2-MeOCH2C5H4N in 15 mL. MeOH and 51 mL. 5% HCl-MeOH with 0.1 g. Pd-C (255 mL. H absorbed) yielded 91% 2-MeC5H4N; or, 2-AcOCH2C5H4N, in a similar way, yielded 88% 2-MeC5H4N. 2-HOCH2C5H4N.HCl (8 g.) added dropwise into 40 g. SOCl2 with cooling, refluxed 2 h., cooled, 100 mL. C6H6 added and the product filtered off gave 8.8 g. 2-ClCH2C5H4N (VII); picrate m. 146-7°. MeONa (2.72 g. Na and 55 mL. MeOH) treated dropwise with VII in 20 mL. MeOH, refluxed 1 h., the solvent removed and the residue extracted with Et2O gave 4.7 g. 2-MeOCH2C5H4N, b18 76-8°. Similarly are prepared (product, b.p./mm. and m.p. picrate given): 3-MeOCH2C5H4N, 92-4°/20, 117-18°; 4-MeOCH2C5H4N, 91-2°/19, 108-9°.

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Product Details of 120099-61-8. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (S)-3-Methoxypyrrolidine, is researched, Molecular C5H11NO, CAS is 120099-61-8, about Ultrapotent vinblastines in which added molecular complexity further disrupts the target tubulin dimer-dimer interface. Author is Carney, Daniel W.; Lukesh, John C. III; Brody, Daniel M.; Brutsch, Manuela M.; Boger, Dale L..

Approaches to improving the biol. properties of natural products typically strive to modify their structures to identify the essential pharmacophore, or make functional group changes to improve biol. target affinity or functional activity, change phys. properties, enhance stability, or introduce conformational constraints. Aside from accessible semisynthetic modifications of existing functional groups, rarely does one consider using chem. synthesis to add mol. complexity to the natural product. In part, this may be attributed to the added challenge intrinsic in the synthesis of an even more complex compound Herein, we report synthetically derived, structurally more complex vinblastines inaccessible from the natural product itself that are a stunning 100-fold more active (IC50 values, 50-75 pM vs. 7 nM; HCT116), and that are now accessible because of advances in the total synthesis of the natural product. The newly discovered ultrapotent vinblastines, which may look highly unusual upon first inspection, bind tubulin with much higher affinity and likely further disrupt the tubulin head-to-tail α/β dimer-dimer interaction by virtue of the strategic placement of an added conformationally well-defined, rigid, and extended C20′ urea along the adjacent continuing protein-protein interface. In this case, the added mol. complexity was used to markedly enhance target binding and functional biol. activity (100-fold), and likely represents a general approach to improving the properties of other natural products targeting a protein-protein interaction.

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthetical and natural phellandrene》. Authors are Kondakoff, Iwan; Schindelmeiser, Iwan.The article about the compound:5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloridecas:148-51-6,SMILESS:OC1=C(C)C(CO)=CN=C1C.[H]Cl).Quality Control of 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride. Through the article, more information about this compound (cas:148-51-6) is conveyed.

Compare Abstract, 1903, i, 845. tert.-Carvomenthyl chloride, obtained from tert.-carvomenthol, boils at 83.5-84.5° under 12 mm. pressure, has a sp. gr. 0.932 at 20°/4°, and forms tert.-carvomenthene, which boils at 174-176°, has a sp. gr. 0.811 at 20°/4°, and nD 1.45709. On treatment with bromine in strongly cooled light petroleum solution, this yields carvomenthene dibromide, which boils between 130° and 144° under 11 mm. pressure, has a sp. gr. 1.208 at 20°/4°, is optically inactive, and by alcoholic potassium hydroxide is converted into a hydrocarbon or mixture of hydrocarbons which must have the constitution (the original abstract includes an equation). This distils in two fractions: the larger boils at 175-180°, has a sp. gr. 0.825 at 20°/4°, and nD 1.46693; the smaller boils at 180-185°, has a sp. gr. 0.828 at 20°/4°, and nD 1.4673. The hydrocarbon is not identical therefore with natural phellandrene. Both fractions are optically inactive and give a red coloration with sulphuric acid in acetic acid solution. A specimen of phellandrene from Phellandrum aquaticum, which boils at 165-168°, has a sp. gr. 0.844 at 20°/4°, nD 1.47575, and [α]D +8°37′ at 20°, reacts with hydrochloric acid in acetic acid solution to form a dextrorotatory chloro-derivative, C10H17Cl, which melts at 110° and boils at 86° under 11 mm. pressure, and a dichloride, C10H18Cl2, which boils at 122.5-125° under 16 mm. pressure, and has a sp. gr. 1.006 at 20°/4° and nD 1.48516 at 20° (compare Pesci, Abstract, 1886, 1038).

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Compounds affecting the development of housefly larvae, published in 1963, which mentions a compound: 148-51-6, mainly applied to , Reference of 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride.

Larval medium (50 g.) was saturated with 100 ml. of water containing 0.5-0.1 g. of the compound and 100 housefly eggs added. After 4 days it was examined for larvae and 3 days later for pupae. Emerging flies laid their eggs on untreated medium after 7 days. A sample of eggs remained in the medium, which was examined for larvae. The flies of this generation were reared to the adult stage. Compounds (245) are listed which are larvicides at 0.5 g. but not at 0.1 g. dosage; 64 compounds are larvicides at a dosage of ≤0.1 g.; 19 cause mortality in the pupal stage. 1,4-Bis(3-hydroxypropionyl)piperazine dimethanesulfonate causes low oviposition or failure of eggs to hatch at 0.05 and 0.025%, low enough to permit some adult emergence.

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia